13338-63-1

Basic information

• Product Name: 3,4,5-Trimethoxyphenylacetonitrile
• Synonyms: (3,4,5-trimethoxyphenyl)-acetonitril;3,4,5-trimethoxybenzeneacetonitrile;3,4,5-trimethoxybenzylnitrile;3,4,5-trimethoxyphenylacetylnitryl;LABOTEST-BB LT00847929;3,4,5-TRIMETHOXYPHENYLACETONITRILE;3,4,5-TRIMETHOXYBENZYL CYANIDE;3,4,5-Trimethoxyphenylacetonit
• CAS NO: 13338-63-1
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• EINECS: 236-388-5
• Product Categories: Aromatic Nitriles;API intermediates;Building Blocks;C10 to C27;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 13338-63-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 77-79 °C(lit.)
• Boiling Point: 346.25°C (rough estimate)
• Flash Point: 132.8 °C
• Appearance: white crystalline powder
• Density: 1.1878 (rough estimate)
• Vapor Pressure: 0.000196mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• BRN: 2214548
• CAS DataBase Reference: 3,4,5-Trimethoxyphenylacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trimethoxyphenylacetonitrile(13338-63-1)
• EPA Substance Registry System: 3,4,5-Trimethoxyphenylacetonitrile(13338-63-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: 3276
• WGK Germany: 3
• RTECS: AM2475000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13338-63-1(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO BEIGE FINE CRYSTALLINE POWDER

Uses

3,4,5-Trimethoxyphenylacetonitrile is used in insecticide compositions.

General Description

3,4,5-Trimethoxyphenylacetonitrile is synthesized by the condensation of 3 : 4 : 5-trimethoxybenzaldehyde with hippuric acid.

InChI:InChI=1/C11H13NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4H2,1-3H3

Synthetic route

Oxime of 3,4,5-trimethoxyphenylpyruvic acid (139109-56-1) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With 1,1'-oxalyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;	88%
With acetic anhydride
With acetic anhydride for 0.0833333h; Heating;

3,4,5-trimethoxyphenyl acetic acid (951-82-6) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 50h;	88%

sodium cyanide (773837-37-9) + 5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 36h;	85%
In acetonitrile Reflux;
In acetonitrile for 4h; Reflux;
In dimethyl sulfoxide

2,3,4-trimethoxybromobenzene (10385-36-1) + acetonitrile (75-05-8) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + Bis-(3,4,5-trimethoxy-phenyl)-acetonitrile (36764-81-5)

Conditions	Yield
With ethoxyethoxyethanol; sodium amide In 1,2-dimethoxyethane 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 4.5 h;	A 83% B 11%

3,4,5-trimethoxybenzyl bromide (21852-50-6) + sodium cyanide (143-33-9) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
In dimethyl sulfoxide Ambient temperature;	75%

3,4,5-trimethoxybenzoyl cyanide (5955-75-9) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With sodium sulfate; ethanethiol; zinc(II) chloride weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol;

(3,4,5-trimethoxy-phenyl)-acetaldehyde-oxime → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With acetic anhydride

Oxime of 3,4,5-trimethoxyphenylpyruvic acid (139109-56-1) + acetic anhydride (108-24-7) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

potassium cyanide (151-50-8) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With water; chloroformic acid ethyl ester; magnesium sulfate Hydrieren des Reaktionsprodukts an Palladium in Benzol;

2,3,4-trimethoxybromobenzene (10385-36-1) + acetonitrile (75-05-8) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With sodium amide 1.) liquid ammonia, 5 min, 2.) liquid ammonia, 15 min; Yield given. Multistep reaction;

potassium cyanide (151-50-8) + 5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
In 1,4-dioxane; water Heating;

4-hydroxy-3,5-dimethoxyphenylacetonitrile (42973-55-7) + dimethyl sulfate (77-78-1) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With potassium carbonate In acetone

sodium cyanide (143-33-9) + 5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With sodium iodide

potassium cyanide (151-50-8) + <3,4,5-trimethoxy-benzyl chloride → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With methanol
With methanol
With ethanol

tetraethylammoniumcyanide (13435-20-6) + 5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
In acetonitrile at 20℃;

(3,4,5-trimethoxyphenyl)methanol (3840-31-1) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / dioxane / 20 °C 2: acetonitrile / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp. 2: 75 percent / dimethylsulfoxide / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: pyridinium chlorochromate / CH2Cl2 / 3 h 2: sodium acetate / acetic anhydride / Heating 3: NaOH / H2O / Heating 4: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 5: acetic anhydride / 0.08 h / Heating View Scheme

3,4,5-trimethoxy-benzaldehyde (86-81-7) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4 / methanol / 20 °C 2: SOCl2 / dioxane / 20 °C 3: acetonitrile / 20 °C View Scheme
Multi-step reaction with 4 steps 1: sodium acetate / acetic anhydride / Heating 2: NaOH / H2O / Heating 3: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 4: acetic anhydride / 0.08 h / Heating View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h / 0 °C 2: thionyl chloride / dichloromethane / 1.5 h / 20 °C 3: dimethyl sulfoxide / 36 h / 20 °C View Scheme

3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / LAH / tetrahydrofuran 2: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp. 3: 75 percent / dimethylsulfoxide / Ambient temperature View Scheme
Multi-step reaction with 6 steps 1: lithium aluminium hydride / diethyl ether / 3 h / Heating 2: pyridinium chlorochromate / CH2Cl2 / 3 h 3: sodium acetate / acetic anhydride / Heating 4: NaOH / H2O / Heating 5: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 6: acetic anhydride / 0.08 h / Heating View Scheme
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: HCl / benzene / 0 °C 3: dioxane; H2O / Heating View Scheme

3-(3,4,5-trimethoxyphenyl)pyruvic acid (61404-52-2) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 2: acetic anhydride / 0.08 h / Heating View Scheme

2-Phenyl-4-(3',4',5'-trimethoxybenzylidene)oxazolone (62616-09-5) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH / H2O / Heating 2: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C 3: acetic anhydride / 0.08 h / Heating View Scheme

3,4,5-Trimethoxybenzoyl chloride (4521-61-3) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: ethanethiol; ZnCl2; Na2SO4 / weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol View Scheme

elemicin (487-11-6) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: ozone; ethyl acetate; oxygen / -15 °C / und anschliessende Hydrierung an Palladium/Calciumcarbonat unter Kuehlung; Isolierung als Natriumhydrogensulfit-Addukt 3: acetic acid anhydride View Scheme

3,4,5-trimethoxyphenylacetaldehyde (5320-31-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 2: acetic acid anhydride View Scheme

1,3-dimethoxy-2-hydroxy-benzene (91-10-1) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2O 2: dimethylformamide 3: K2CO3 / acetone View Scheme

2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol (39667-14-6) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide 2: K2CO3 / acetone View Scheme

5-(chloromethyl)-1,2,3-trimethoxybenzene (3840-30-0) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
In water; ethyl acetate; N,N-dimethyl-formamide

trimethylsilyl cyanide (7677-24-9) + 3,4,5-trimethoxybenzyl bromide (21852-50-6) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In acetonitrile Reflux;
With tetra-n-butylammoniumfluoride trihydrate In acetonitrile for 6h; Reflux;
With tetrabutyl ammonium fluoride In acetonitrile for 6h; Reflux;
With tetrabutyl ammonium fluoride In acetonitrile for 6h; Reflux;

3,4,5-trihydroxybenzoic acid (149-91-7) → 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice 3: phosphorus tribromide / dichloromethane / 4 h / Cooling with ice; Inert atmosphere 4: tetra-n-butylammoniumfluoride trihydrate / acetonitrile / 6 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 3: phosphorus tribromide / dichloromethane / 0 - 20 °C 4: tetrabutyl ammonium fluoride / acetonitrile / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 4.5 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice 4: tetrabutyl ammonium fluoride / acetonitrile / 6 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 4.5 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice 3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice 4: tetrabutyl ammonium fluoride / acetonitrile / 6 h / Reflux View Scheme

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + formic acid ethyl ester (109-94-4) → 3-hydroxy-2-(3,4,5-trimethoxyphenyl)acrylonitrile sodium salt

Conditions	Yield
With sodium methylate In methanol for 2h; Heating;	98%

4-phenyl-butan-1-ol (3360-41-6) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → C21H25NO3

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;	98%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 4-hydroxy-benzaldehyde (123-08-0) → C18H17NO4

Conditions	Yield
With sodium ethanolate In ethanol at 20 - 85℃; for 3h; Inert atmosphere;	97%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + hexan-1-ol (111-27-3) → 2-(3,4,5-Trimethoxy-phenyl)-octanenitrile (108781-06-2)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;	97%

3-(pyridin-2-yl)-propanol (2859-68-9) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → C19H22N2O3

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;	96%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + Diphenylphosphine oxide (4559-70-0) → (3,4,5-trimethoxybenzyl)diphenylphosphine oxide (159386-48-8)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium tert-butylate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine In 1,4-dioxane at 120℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Schlenk technique;	96%
With potassium tert-butylate; nickel dichloride In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; Schlenk technique;	71%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + O-methoxymethylisovanillin (5779-98-6) → (Z)-3-(4-Methoxy-3-methoxymethoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-acrylonitrile

Conditions	Yield
With sodium hydroxide; Aliquat 336 In dichloromethane for 4h; Ambient temperature;	95%

3-iodo-4-methoxybenzaldehyde (2314-37-6) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → C19H18INO4 (1408251-07-9)

Conditions	Yield
With sodium methylate In methanol at 45℃;	93%

p-methylcyclohexanol (589-91-3) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → C18H23NO3

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 10h; Inert atmosphere; Green chemistry;	93%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → 3,4,5-trimethoxyphenyl acetic acid (951-82-6)

Conditions	Yield
With potassium hydroxide Heating;	92%
With sulfuric acid; acetic acid In water for 22h; Reflux;	82%
With hydrogenchloride
With potassium hydroxide In ethanol Reflux;
With water; potassium hydroxide In ethanol for 15h; Reflux;

2-Aminonicotinaldehyde (7521-41-7) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → 3-(2,3,4-trimethoxyphenyl)-[1,8]naphthyridin-2-ylamine (1075240-58-2)

Conditions	Yield
With aminosulfonic acid for 0.05h; microwave irradiation;	92%

ethanol (64-17-5) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → Ethyl 3,4,5-Trimethoxyphenylacetimidate Hydrochloride (93270-42-9)

Conditions	Yield
With hydrogenchloride Ambient temperature;	91%
With hydrogenchloride In benzene	82%
With hydrogenchloride In chloroform for 2h; Ambient temperature;
With hydrogenchloride In diethyl ether at 0℃;
With hydrogenchloride In diethyl ether

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + cyclohexanone (108-94-1) → (1-hydroxy-cyclohexyl)-(3,4,5-trimethoxy-phenyl)-acetonitrile

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 0 - 15℃; for 1h;	90%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (Z)-2-(3,4,5-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)acrylonitrile

Conditions	Yield
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;	90%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → ethyl 3,4,5,-trimethoxy-α-cyanobenzeneacetate (62038-54-4)

Conditions	Yield
	89%
	89%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + dimethyl sulfate (77-78-1) → 2-methyl-2-(3,4,5-trimethoxyphenyl)propanenitrile (19589-24-3)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -30 - 20℃;	88%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + (4-ethoxyphenyl)boronic acid (22237-13-4) → 1-(4-ethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one

Conditions	Yield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;	87%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 3-fluoro-4-methoxy-phenylboronic acid (149507-26-6) → 1-(3-fluoro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions	Yield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;	85%

1-ethynyl-2-methylbenzene (766-47-2) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → (Z)-4-(o-tolyl)-2-(3,4,5-trimethoxyphenyl)but-2-enenitrile

Conditions	Yield
With potassium tert-butylate; tert-butyl alcohol In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; stereoselective reaction;	84%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 4-methylphenylboronic acid (5720-05-8) → 1-(p-tolyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions	Yield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;	84%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + naphthalene-2-boronic acid (32316-92-0) → 1-(naphthalen-2-yl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions	Yield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;	84%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + cyclohexanol (108-93-0) → C17H21NO3

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 10h; Inert atmosphere; Green chemistry;	83%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 4-Methoxybenzyl alcohol (105-13-5) → (E)-3,4,4',5-tetramethoxystilbene (134029-62-2)

Conditions	Yield
With C15H25Cl2N3NiO3; potassium tert-butylate In octane at 120℃; for 24h; Schlenk technique; Inert atmosphere;	83%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 4-methoxy-benzaldehyde (123-11-5) → (Z)-2-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile

Conditions	Yield
With sodium methylate In methanol at 20℃; Reflux;	82%
With sodium hydroxide; Aliquat 336 In dichloromethane for 4h; Ambient temperature;	75%
Stage #1: 2-(3,4,5-trimethoxyphenyl)acetonitrile; 4-methoxy-benzaldehyde In methanol at 60℃; for 0.5h; Stage #2: With sodium methylate In methanol at 60℃;

methanol (67-56-1) + 2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) → α-methyl-3,4,5-trimethoxybenzeneacetonitrile (91641-41-7)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;	82%

2-(3,4,5-trimethoxyphenyl)acetonitrile (13338-63-1) + 4-methoxyphenylboronic acid (5720-07-0) → 1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one (203058-56-4)

Conditions	Yield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;	82%

Upstream product

• 5955-75-9 3,4,5-trimethoxybenzoyl cyanide 
• 21852-50-6 3,4,5-trimethoxybenzyl bromide 
• 143-33-9 sodium cyanide 
• 10385-36-1 2,3,4-trimethoxybromobenzene 
• 75-05-8 acetonitrile 
• 42973-55-7 4-hydroxy-3,5-dimethoxyphenylacetonitrile 
• 77-78-1 dimethyl sulfate 
• 151-50-8 potassium cyanide 
• 13435-20-6 tetraethylammoniumcyanide 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 
• 61404-52-2 3-(3,4,5-trimethoxyphenyl)pyruvic acid 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 773837-37-9 sodium cyanide 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 101-30-4 2-(3,4,5-trimethoxy-benzyl)-4,5-dihydro-1H-imidazole 
• 77252-99-4 (6-Methyl-pyridin-2-yl)-(3,4,5-trimethoxy-phenyl)-acetonitrile 
• 33735-05-6 N-(3,3,3-Triphenyl-propyl)-benzamide 
• 94559-44-1 4-(Benzoylamino)-2-(3,4,5-trimethoxyphenyl)butyronitril 
• 94559-45-2 N,N'-<3-Cyan-3-(3,4,5-trimethoxyphenyl)-1,5-pentadiyl>bisbenzamid 
• 93270-42-9 Ethyl 3,4,5-Trimethoxyphenylacetimidate Hydrochloride 
• 144037-94-5 2,3,4,5-Tetramethyl-6-(3,4,5-trimethoxy-benzyl)-benzonitrile 
• 116377-23-2 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-methylanisole 
• 124619-44-9 2-Amino-4-methoxybenzyl methyl ether 
• 124619-07-4 (5-Methoxy-2-methoxymethyl-phenyl)-(3,4,5-trimethoxy-phenyl)-acetonitrile 
• 124619-15-4 (2-Methoxy-5-methoxymethyl-phenyl)-(3,4,5-trimethoxy-phenyl)-acetonitrile 
• 116377-16-3 2-cyano-3-(3',4',5'-trimethoxybenzyl)-4-(methoxymethyl)anisole 
• 124619-23-4 α-(3',4',5'-trimethoxyphenyl)-2-(methoxymethyl)-4,5-(methylenedioxy)phenylacetonitrile 
• 129319-52-4 α-(3',4',5'-trimethoxyphenyl)-2,6-dimethoxy-3-(methoxymethyl)-3-pyridylacetonitrile 

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Combretastatin A4 analogue containing cyanoethylene joining chain and application in preparing antitumor drugs

The invention a Combretastatin A4 analogue containing a cyanoethylene joining chain and an application in preparing antitumor drugs, which relates to the field of a medicinal compound. A structural formula (I-IV) is shown as the specification, an anticancer candidate compound which has strong inhibitory activity against cancer cells and is not toxic to normal cells is currently lacked, for the reason, the method prepares 19 I-IV series compounds, and the para and meta positions of the B ring (benzene ring) introduce various alkyl groups, alkoxy groups or amino substituents or replace the B ring (benzene ring) with various heterocyclic rings. In the I-series compound, when the para position of the B ring (benzene ring) is substituted with an ethyl group, an isopropyl group, a dimethylaminogroup or a diethylamino group, the proliferation resistance of the cancer cells is very strong, and toxicity is weak for the L-02 normal cells, a selective anticancer activity coefficient (an IC50 value ratio of L-02 normal cells to cancer cells) can even exceed 10,000, and the four compounds have the potential to be developed into safe and highly effective anticancer drugs.

Synthesis and characterisation of (Z)-styrylbenzene derivatives as potential selective anticancer agents

To identify anticancer agents with high potency and low toxicity, a series of (Z)-styrylbenzene derivatives were synthesised and evaluated for anticancer activities using a panel of nine cancer cell lines and two noncancerous cell lines. Most derivatives exhibited significant anti-proliferative activities against five cancer cell lines, including MGC-803 and BEL-7402. (Z)-3-(p-Tolyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile (6h) showed a strong inhibitory effect on MGC-803 cells (IC50 50 50 value of 6h in L-02 cells was 10,000-fold higher than in MGC-803 cells. Compound 6h inhibited proliferation of BEL-7402 cells by arresting at the G2/M phase through up-regulation of cyclin B1 expression, down-regulation of cyclin A and D1 expression, and induction of apoptosis. In addition, 6h inhibited the migration of BEL-7402 cells and the formation of cell colonies.

TYD1608 with selective anti-cancer activity as well as preparation and application thereof

The invention provides cyan-containing TYD1608, i.e., (Z)-3-(p-methyl phenyl)-2-(3,4,5-trimethoxyphenyl) acrylonitrile as well as preparation and application thereof, and relates to the field of medicinal compounds with the structure shown in the description. Various anti-cancer medicine in the prior art have the killing capability on cancer cells and also have great toxicity on normal cells; thetreatment of cancer patients is seriously influenced, so that the invention of the medicine with the selective anti-cancer activity on the normal cells is very important. The TYD1608 is synthesized; the compound shows strong proliferation inhibition capability on six kinds of human face cancer cells; in addition, the toxicity on the L-02 normal human liver cells is weak. The IC50 value on the MGC-803 gastric cancer cells is smaller than 0.01 mu M, is better than the clinic common use anti-cancer medicine of taxol; good selective anti-cancer activity is realized. Mechanism study shows that theproliferation inhibition activity of the TYD1608 on BEL-7402 cancer cells is the result of inhibiting the G2/M period in the cell period, inducting early stage and later stage apoptosis, blocking cellmigration, inhibiting cell period relevant protein cyclin A1 and cyclin D1.